Surface treatment composition and process

ABSTRACT

The invention relates to a composition comprising a compound of formula (I): R f —B—Ro—Z and a compound of formula (II): 
                         
and/or their reaction product.

The present invention relates to the area of surface treatments. It hasas an objective, a composition and process for surface treatment ofsubstrates using said composition. The invention also has as anobjective, a compound and the process for its preparation. Furthermore,the invention has as an objective, substrates which may be obtained bysaid surface treatment process.

In all areas such as construction, furniture, home appliances, soilingof the surfaces is deleterious, both from the hygienic and aestheticpoint of view. In areas such as transportation, particularly inairplanes or cars, the accumulation of dirt can also present asignificant hazard such as causing poor vision through transparentsurfaces. It then is necessary to expend effort to re-establish aminimum level of cleanliness which entails costs.

Surface treatment for substrates are known which improve theirproperties, notably by decreasing dirt retention.

The degree of dirt retention is generally attributed to the wettabilityof the substrates by polar or non-polar liquids. The wettability of asubstrate is characterized by the contact angle formed by a drop ofliquid on the substrate. Thus a large angle, notably above 90°,indicates that the substrate is not wetted by the liquid.

Numerous hydrophobic and oleophobic treatments have been proposed overthe last few years.

Thus, U.S. Pat. No. 5,523,161 discloses a glass substrate having lowwettability obtained by treatment with a perfluoroalkylalkylsilane. Thetreatment is rendered more durable by mixing theperfluoroalkylalkylsilane with silanes capable of being hydrolyzed.

Such perfluoroalkylalkysilane films are also described in the documentEP 692 463. The abrasion resistance is improved by depositing thesefilms onto an inorganic sub-layer.

Patent application WO 99/18168 describes a coating composition withimproved resistance to abrasion and to UV radiation containing a mixtureof alkoxysilane and halogenosilane.

Finally, EP 491 251 and EP 492 545 disclose monomolecular films fromperfluoroalkylalkylsilanes which may have an ether, ester or carbonylfunction between the perfluoroalkyl group and the alkyl group.

These proposed anti-soil treatments confer to the treated substrateproperties of low wettability by polar and non-polar liquids, i.e. bothhydrophobic and oleophobic properties. Such liquids thus form drops witha high contact angle.

It has been observed that substrates which have been subjected to suchtreatments can present spots and rings which are difficult to wash off.The soiling results from small soil-containing drops which dry anddeposit the soil they contain.

Currently proposed systems for treating substrates based on a largeliquid contact angle are thus not completely satisfactory.

There is a need for a surface treatment which overcomes the deficienciesdescribed above.

These deficiencies have been overcome by the present invention's surfacetreatment which confers on the substrate improved resistance to soilingresulting from greases and oils. It has been surprisingly observed thatapplication to a substrate of a composition comprising a silane havingperfluorinated groups and polar groups yielded very satisfactoryresults.

In addition, a substrate so treated presented a self-cleaning character.The term “self-cleaning character” means easy cleaning of a soiledsubstrate, for example by a simple stream of water without additionalmechanical assistance.

An objective of the invention is thus a composition comprising acompound of formula (I):R_(f)—B—Ro—Z  (I)in which:

-   -   R_(f) represents a perfluorinated alkyl radical with a straight        or branched chain comprising 1 to 20 carbon atoms, preferably 6        to 16 carbon atoms;    -   B represents a bivalent group which may comprise 1 to 3 atoms of        oxygen, sulfur and/or nitrogen;    -   Ro represents 1 to 100, preferably 5 to 20 oxyalkylene groups,        preferably oxyethylene or oxypropylene groups connected to the        group B via a carbon atom; and    -   Z is a hydrogen atom or, when B carries a hydroxyl group, a        linear or branched chain alkyl group comprising 1 to 6 carbon        atoms;        and a compound of formula (II)

in which:

-   -   m is a whole number from 0 to 10, preferably 0 to 3;    -   R represents, each independently from the other, a linear or        branched alkyl group comprising 1 to carbon atoms;    -   p is a whole number from 0 to 2, preferably 0;    -   A represents, each independently from the other, a halogen,        preferably chlorine, or an alkoxy group comprising 1 to 6 carbon        atoms, preferably methoxy, ethoxy, propyloxy, and/or        isopropyloxy; and    -   Y represents a group comprising an isocyanate; epoxy, carboxylic        acid or alcohol function, Y can so represents Si(R_(p))(A)_(3-p)        when m is different from zero, and a group A when m is equal to        zero;        and/or the reaction product.

Preferably, compound (II) is chosen among the well known non-ionicfluorinated surface active agents, for example FORAFAC® 1110D fromATOFINA or ZONYL® FSN or FSO from DuPont or UNIDYNE DS 401 from Daikin.The compound for formula (I) can be a primary or secondary alcohol. Thesecondary alcohol can be obtained, for example, by reaction of afluorinated epoxide with a polyglycol ether such asCH₃O(C₂H₄O)_(n)—C₂H₄OH.

The preferred compounds of formula (II) are derivatives presenting anisocyanate or epoxy function. Examples of such compounds areγ-isocyanatopropyltriethoxysilane (SILQUEST A 1310 a silane from Witco),COATOSIL 1770 from Witco or glycidyl-3-oxypropyl-triethoxysilane (GLYEOfrom Huls/Sivento).

Such a composition is particularly useful to treat the surface ofsubstrates. To this end, the composition contains, in combination withan anhydrous solvent, 1 to 50%, and in particular 10 to 40% by weightthe compounds of formula (I) and (II) and/or of their reaction product.Appropriate anhydrous solvents are, for example, esters such as ethyl,butyl or isopropyl acetates, ketones such as acetone, methylethylketoneor methylisobutylketone.

Advantageously, the composition may comprise several compounds from eachcategory. The composition may also contain the usual additives.

According to another embodiment of the invention, this composition maybe diluted by introduction of another solvent chosen among water, thealcohols and their mixtures. Such a composition may comprise 0.05 to 5%,in particular 0.1 to 2% by weight of the cited compounds.

According to a specific embodiment, the composition is in the form of anaqueous emulsion.

The invention also has as an objective a process for preparing such acomposition. This comprises the step of:

-   (a) dissolving a compound of formula (I) and a compound of    formula (II) in an appropriate anhydrous solvent.

According to a specific embodiment, alkoxysilane or halogenosilanefunctions and a hydrolysis agent such as water are added for thehydrolysis. The process then comprises the following additional step:

-   (b) addition of a solvent chosen among water, the alcohols or their    mixtures.

According to a particular embodiment, the process also comprises thefollowing additional steps:

-   (c) emulsification of the solution obtained in step (b), if    necessary in the presence of a surface active agent or a water    soluble polymer; and if necessary,-   (d) separation of the anhydrous solvent.

The invention also has as an objective a compound, of formula (III)

in which Rf, B, Ro, m, A and p are as defined above and Q is acarbamate, ester, alkoxysilane or ether function, preferably a carbamateor ether function.

The compound of formula (III) may be obtained notably by reaction of thealcohol function in a compound of formula (I) with the group Y in thecompound of formula (II), if necessary in the presence of a catalyst.

In this embodiment of the invention, it is important to avoid hydrolysisof the alkoxysilane or halogenosilane groups, notably by operating in ananhydrous medium. Hydrolysis of these groups leads crosslinking of thesilane. Appropriate conditions can easily be determined by those skilledin the art. The addition of a catalyst for the reaction may beadvantageous.

The solution of the compound in the synthesis solvent constitutes apreferred embodiment of the invention. Such a composition is obtaineddirectly after synthesis and does not require a subsequent separation.

The compound of formula (III) can be isolated in the form of a powder, apaste or a liquid, by total elimination of the synthesis solvent andincorporation into other solvents or compositions. Preferably, thecompound is introduced into an appropriate anhydrous solvent such as,for example, a solvent chosen among the esters such as ethyl, butyl orisopropyl acetates, ketones such as acetone, methylethyl-ketone ormethylisobutylketone. Such a composition can be stored for extendedperiods of time.

According to another embodiment of the invention, the compound (III) canbe synthesized in situ at the time of application of a compositionaccording to the invention comprising its precursors.

The chemical nature of the layer formed is less well defined to theextent that crosslinking of hydrolyzed compounds (I) and (II) leads to acompound of formula (III) as well as other products. However, thisembodiment leads to results of comparable quality and also presents theadvantage of reducing the number of steps required in the preparation.

Another embodiment of the invention relates to a composition of theinvention comprising, in addition, other solvents such as water and/oralcohols such as methanol, ethanol or isopropanol, preferably ethanol orisopropanol. Preferably, a mixture of alcohol and water is used. Thesecompositions are notably useful as ready for use compositions.

The water added is important as a hydrolysis agent for the alkoxysilaneor halogenosilane groups. The alcohols generally represent good solventsfor the products contained in the composition.

These compositions can be obtained, for example, by dilution of acomposition comprising and anhydrous solvent in a water-alcoholsolution. The water-alcohol solution contains 0 to 100%, preferably 10to 90% by weight of alcohol. The addition of an organic or inorganicacid such as those chosen among acetic acid or hydrochloric acid isadvantageous because it catalyzes the hydrolysis of the halogenosilaneor alkoxysilane functions.

The composition in an anhydrous solvent may also be diluted in water. Inthis case, it may be advantageous to work in the presence of one or moresurface active agents and/or one or more water-soluble polymers. Thesolution is strongly agitated, for example using a high pressurehomogenizer, then distilled to eliminate all or part of the anhydroussolvent. A stable aqueous emulsion is so obtained.

The reactions which occur when the composition is applied to a substrateare not precisely known. It appears however that the alkoxysilane orhalogenosilane groups present in the composition are hydrolyzed underthe effect of the hydrolysis agent into Si—OH groups, which can reacttogether and also with Si—OH groups in the glass. The latter reaction isdesignated as a chemical adsorption reaction of the chemical layerdeposited on the substrate. The silane groups can also reactintermolecularly to form a three dimensional network comprising Si—O—Sibonds, thus conferring a high level of hardness to the deposited layer.

Another objective of the invention relates to a process for treating thesurface of a substrate, comprising the step of:

-   (i) applying a composition of the invention to the substrate being    treated in the presence of a hydrolysis agent for the alkoxysilane    or halogenosilane groups present.

The substrates are preferably carefully cleaned before the surfacetreatment. Such a cleaning significantly improves the adhesionproperties, for example by activating the hydroxyl functions on thesurface of a glass substrate. In the case of glass substrates, it hasbeen found advantageous to immerse them in a chromic acid solutionfollowed by washing with demineralized water and drying.

The composition applied to the substrate can already contain ahydrolysis agent such as water, for example be in the form of awater-alcohol solution or an aqueous emulsion. A hydrolysis catalystsuch as an organic or inorganic acid can also be added if desired.

The composition applied can also be in the form of a solution in ananhydrous solvent. In this case, the humidity in the air acts as ahydrolysis agent. The composition as described can be applied to thesubstrate using appropriate and known techniques, for example byspraying, brushing, coating, impregnation, immersion, at a concentrationfrom 0.05 to 5%, preferably 0.1 to 2% active material.

A thermal treatment may be applied depending on the substrate. Thus,advantageously, but optionally, the process comprises an additional stepof:

-   (ii) thermal treatment of the substrate after step (i) at a    temperature comprised between 50 and 200° C. for a period of time    comprised between 1 second and 24 hours.

Preferably, the process is carried out using water as the hydrolysisagent.

In general, the thermal treatment is shorter the higher the temperature.The primary purpose of this thermal treatment is to evaporate thesolvent. Thus, it is recommended when the solvent has an elevatedevaporation temperature.

It is also possible for the hydrolysis agent to be present on thesubstrate to which the composition is applied.

The invention further has as an objective a substrate obtained by theprocess described above.

Such substrates are in general inorganic or organic substrates made fromtransparent material, on which traces of dried drop residues are mostannoying. These substrates can be subjected to another surfacetreatment, for example an anti-reflection treatment, before beingsubjected to the surface treatment of the invention. The materialsinvolved are, for example, glass, polymethyl methacrylate andpolycarbonate, and also any type of material such as stone, brick,concrete, wood, tile, leather or textiles.

The substrates treated in accordance with the process of the inventionhave a good resistance to oils and self-cleaning properties.

The following examples illustrate the invention without limiting it.

EXAMPLE 1

20 parts of oxyethylated fluorinated alcohol FORAFAC 1110 having thestructure C₆F₁₂C₂H₄O(CH₂—CH₂O)_(n)H, where n has an average value of 11,are introduced into a 250 ml three-necked flask equipped with atemperature probe and a condenser connected to the atmosphere via aCaCl₂ trap. This compound was synthesized by action of ethylene oxide onthe alcohol C₆F₁₃C₂H₄OH using BF₃/ether catalysis. The dioxane producedas a by-product of the reaction was eliminated using toluene and thendistilled. The oxyethylated alcohol was diluted with 42 grams ofanhydrous ethyl acetate, then the catalyst was added: 0.2 partsdibutyldilaurate tin. The reaction medium was rendered inert using ananhydrous nitrogen sweep and the solution was heated under reflux at 77°C., then a stoichiometric quantity (relative to the OH group) of3-(triethoxy)silylpropylisocyanate, of formula (C₂H₅O)₃Si(CH₂)₃—N═C═O,was introduced, i.e. 7.9 parts. The reaction was followed by analyzingfor the N═C═O using FTIR spectrometry; it is completed in 3 hours.

A solution S1 was obtained containing 40% of active material having thefollowing structure:

C₆F₁₃C₂H₄O(CH₂—CH₂O)_(n)—OC(O)NH—(CH₂)₃—Si(OC₂H₅)₃ where n has anaverage value of 11.

EXAMPLE 2

This example describes the preparation of a composition for the in situsynthesis of the compound during application. 18 parts of oxyethylatedfluorinated alcohol FORAFAC 1110 having the structureC₆F₁₃C₂H₄O(CH₂—CH₂O)_(n)H, where n has an average value of 11, areintroduced into a 125 ml flask, dissolved in 55 parts of ethyl acetateand 18 parts of tetraethoxysilane Si(OC₂H₅)₄ from Aldrich are added. Asolution S2 (40% dry extract) of a ready for use bi-component mixture isobtained.

EXAMPLE 3

This example describes the preparation of a composition for the in situsynthesis of the compound during application. 25 parts of oxyethylatedfluorinated alcohol FORAFAC 1110 having the structureC₆F₁₃C₂H₄O(CH₂—CH₂O)_(n)H,where n has an average value of 11, are introduced into a 125 ml flask,dissolved in 55 parts of ethyl acetate and 12 parts of a silane epoxideCoatasil 1770 from WITCO having the structure:

are added.

A solution S3 (40% dry extract) of a ready for use bi-component mixtureis obtained.

EXAMPLE 4

This example describes the preparation of a composition for the in situsynthesis of the compound during application. 25 parts of oxyethylatedfluorinated alcohol FORAFAC 1110 having the structureC₆F₁₃C₂H₄O(CH₂—CH₂O)_(n)H,where n has an average value of 11, are introduced into a 125 ml flask,dissolved in 55 parts of ethyl acetate and 11.7 parts of a silaneepoxide GLYEO from HULS/SIVENTO having the structure:

are added.

A solution S4 (40% dry extract) of a ready for use bi-component mixtureis obtained.

EXAMPLE 5

20 parts of an addition product from perfluoroalkyl and hydroxylatedethylene oxide, UNIDYNE DS 401 from DAIKIN of formula(CF₃)₂CF(CF₂)_(n)CH₂CHOHCH₂O(C₂H₄)_(n).CH₃ with n=6/8/10 and n′≈8 and 50parts of ethyl acetate are introduced into a 100 ml three-necked flaskequipped with a temperature probe, a condenser and a drop funnel. Thereaction medium was rendered inert using an anhydrous nitrogen sweep andthe solution was heated under reflux at 77° C., then traces of waterfrom the surface active agent were eliminated by azeotropic distillation0.2 parts dibutyldilaurate tin were added, then a stoichiometricquantity (relative to the OH group) of3-(triethoxy)silylpropylisocyanate, of formula (C₂H₅O)₃Si(CH₂)₃—N═C═O,was introduced, i.e. 4.6 parts. The reaction was followed by analyzingfor the N═C═O using FTIR spectrometry; it is completed in 2 hours.

A solution S5 was obtained containing 33% of active material having thefollowing formula:

COMPARATIVE EXAMPLE 1

19.4 parts of fluorinated thiol of formula C₈F₁₇C₂H₄SH and 5 parts ofanhydrous ethyl acetate are introduced into a 100 ml three-necked flaskequipped with a temperature probe, a condenser connected to theatmosphere via a CaCl₂, trap and a drop funnel.

The reaction medium was rendered inert using an anhydrous nitrogen sweepand the solution was heated under reflux at 77° C., then the drop funnelwas used to introduce over 5 hours a solution containing 10 parts2-(trimethoxy)silylpropyl methacrylate (MEMO) of formulaCH₂═C(CH)₃C(O)O(CH₂)₃Si(OCH₃)₃ and 0.3 parts of AIBN initiator, dilutedwith 40 parts of anhydrous ethyl acetate.

The solution SC1 obtained contains 39.5% of the mono-addition product offormula: C₈F₁₇C₂H₄S—CH₂—C(CH)₃C(O)O(CH₂)₃Si(OCH₃)₃.

COMPARATIVE EXAMPLE 2

45 parts of an oxyethylated surface active agent, BRIJ 76 from ICI (offormula CH₃(CH₂)₁₇(OC₂H₄)₁₀OH and 50 parts of anhydrous ethyl acetateare introduced into a 100 ml three-necked flask equipped with atemperature probe, a condenser and a drop funnel. The reaction mediumwas rendered inert using an anhydrous nitrogen sweep and the solutionwas heated under reflux at 77° C., then traces of water from the surfaceactive agent were eliminated by azeotropic distillation. 0.1 partsdibutyldilaurate tin were added, then a stoichiometric quantity(relative to the OH group) of 3-(triethoxy)silylpropylisocyanate, offormula (C₂H₅O)₃Si(CH₂)₃—N═C═O, was introduced, i.e. 17.1 parts. Thereaction was followed by analyzing for the N═C═O using FTIRspectrometry; it is completed in 5 hours.

A solution SC2 was obtained containing 55% of active material having thefollowing structure: CH₃(CH₂)₁₇(OC₂H₄)₁₀OCONH—(CH₂)₃—Si(OC₂H₅)₃

The solutions S1, S2, S3, S4, S5, SC1 and SC2 obtained in the exampleswere then diluted in a mixture of water/isopropanol (ratio 10/90) andadjusted to a pH 5 with acetic acid. Solutions containing 0.1% by weightactive materials were obtained.

These solutions were then applied to inorganic glass plates (slides)used for optical microscopy which were previously cleaned by immersionin chromic acid solution and then washed with demineralized water anddried. The glass plates so prepared were then immersed in aqueoussolutions containing 0.1% active material for 1 hour at ambienttemperature, then pulled put vertically at 0.5 mm/minute using a KRUSStensiometer, and finally dried for 1 hour at 60° C. in an oven.

The oil resistance and the washability of the glass plates treated inthis manner were then evaluated.

The following tests were used to evaluate the performance of thesubstrates treated in accordance with the invention:

Oil Resistance (Oleophobic Character)

The oil resistance is characterized by measuring the contact angle ofdrops of paraffin oil, dodecane and tetradecane deposited on the treatedsubstrate. A comparative measurement is carried out on an untreatedglass plate. The angle is measured using an ERMA G1 type goniometer.

A small volume drop (≈1.5 μL) of oil is deposited on the treatedsubstrate using a syringe controlled by a micrometer screw. Thesubstrate is maintained horizontal on a platen whose horizontal positionis controlled by a bubble level. The angle is measured at the twotangents to the points of contact of the drop on the substrate. Theaverage of these two angles on at least four drops is calculated.

Self-cleaning or Washability Test

The self-cleaning character is determined using a variant of theso-called “spray test” described in standard AATCC 22-1989 whichinvolves mounting a substrate according to the invention which has beensoiled onto a support inclined at 45″, then pouring 50 ml of water froma funnel providing with a watering pump over a period of about 5 secondsfrom a height of about 20 cm.

The substrates obtained by treatment with the solutions of the inventionand of the comparative examples are previously soiled by spraying withparaffin oil which has been colored red using an organol type dye. Thedeposit is of the order of 30 g/m². Water is dropped on the sample asdescribed above and it is visually examined. The persistance of coloredoil spots is noted as well as the presence of residual water drops.

The results are given in the following table.

Comparative example 1 is an alkoxysilane carrying a perfluorinated groupand also an ester and thioether group. It has a strongly oleophobiccharacter as seen from the contact angles measured relative to thenon-polar liquids. It is possible to observe the appearance of small oildroplets as soon as the substrate is sprayed with the colored oil.However, this type of treatment does not allow elimination of the soilby simple passage of water. In fact, small colored spots remain whichpresumably are derived from drying of small droplets containingimpurities.

Comparative example 2 relates to a compound which carries hydrophilicgroups but no perfluorinated groups. It is seen from the small contactangles measured that this compound is oleophilic. It is in fact observedthat the substrate is wetted by paraffin oil without formation ofdroplets. In addition, the substrate has a hydrophilic nature. However,this property is not sufficient since it is possible to observe coloredtracks after passage of water.

The test on untreated glass shows the unsatisfactory behavior of asubstrate having an oleophilic and hydrophobic character.

θ (°) θ (°) θ (°) paraffin oil dodecane tetradecane WashabilityTreatment (° C.) (° C.) (° C.) Spots Water drops S1 61 52 59 − − SC1 8273 79 +++ ++ SC2 <20 <20 <20 +++ + S2 61 44 50 − − S3 61 46 54 − − S4 6152 56 − − S5 n.d. n.d. n.d. − − Untreated <20 <20 <20 ++ +++ glass −:practically no visible spot or drop +: a few visible spots or drops ++:more numerous visible spots or drops +++: very numerous visible spots ordrops n.d.: not determined

In contrast, it can clearly be seen that the substrates treated withcompositions of the invention yield very satisfactory results, namelythe near absence of colored paraffin oil spots and also of small waterdroplets which may later reinforce the appearance of dirt on thesubstrate.

Thus, the compositions of the invention provide an effective anti-soiltreatment for substrates, consisting in an elimination of dirt by simplepassage of water.

1. A composition comprising a compound of formula (I):R_(f)—B—Ro—Z  (I) in which: R_(f) represents a perfluorinated alkylradical with a straight or branched chain comprising 1 to 20 carbonatoms; B represents a bivalent group which may comprise 1 to 3 atoms ofoxygen, sulfur and/or nitrogen; Ro represents 1 to 100 oxyalkylenegroups connected to the group B via a carbon atom; and Z is a hydrogenatom or, when B carries a hydroxyl group, a linear or branched chainalkyl group comprising 1 to 6 carbon atoms; and a compound of formula(II)

in which: m is a whole number from 0 to 10; R represents, eachindependently from the other, a linear or branched alkyl groupcomprising 1 to 6 carbon atoms; p is a whole number from 0 to 2; Arepresents, each independently from the other, a halogen, or an alkoxygroup comprising 1 to 6 carbon atoms; and Y represents a groupcomprising an isocyanate, epoxy, carboxylic acid or alcohol function, Ycan also represent Si(R_(p))(A)_(3-p) when m is different from zero, anda group A when m is equal to zero; and/or their reaction product. 2.Composition according to claim 1, in which R_(f) in formula (I)comprises 6 to 16 carbon atoms.
 3. Composition according to claim 1, inwhich Ro in formula (I) represents 5 to 20 oxyalkylene groups. 4.Composition according to claim 1, in which m in formula (II) is a numberfrom 0 to
 3. 5. Composition according to claim 1, in which Y in formula(II) comprises an isocyanate or epoxy function.
 6. Composition accordingto claim 1, in which A in formula (II) represents a methoxy, ethoxy,propyloxy, and/or isopropyloxy group.
 7. Composition according to claim1, in which p is
 0. 8. Composition according to claim 1, comprising 1 to50% by weight of the compounds of formula (I) and (II) and/or thereaction product thereof.
 9. Composition according to claim 1,comprising in addition a solvent chosen among water, the alcohols andtheir mixtures.
 10. Composition according to claim 1 comprising 0.05 to5% by weight of active material.
 11. Composition according to claim 1 inthe form of an aqueous emulsion.
 12. Process for preparing a compositionaccording to any claim 1 comprising the step of: (a) dissolving acompound of formula (I) and a compound of formula (II) in an anhydroussolvent.
 13. Process according to claim 12, comprising the followingadditional step: (b) addition of a solvent chosen among water, analcohol or their mixtures.
 14. Process according to claim 13, comprisingthe following additional steps: (c) emulsification of the solutionobtained in step (b), if necessary in the presence of a surface activeagent or a water soluble polymer; and if necessary, (d) separation ofthe anhydrous solvent.
 15. Compound of formula (III)

in which: m is a whole number from 0 to 10; R_(f) represents aperfluorinated alkyl radical with a straight or branched chaincomprising 1 to 20 carbon atoms; B represents a bivalent group which maycomprise 1 to 3 atoms of oxygen, sulfur and/or nitrogen; Ro represents 1to 100 oxyalkylene groups connected to the group B via a carbon atom; Rrepresents, each independently from the other, a linear or branchedalkyl group comprising 1 to 6 carbon atoms; p is a whole number from 0to 2; A represents, each independently from the other, a halogen, or analkoxy group comprising 1 to 6 carbon atoms; and Q is a carbamate,ester, alkoxysilane or ether function.
 16. Compound according to claim15 in which Q is a carbamate or ether function.
 17. Process forpreparing a compound of claim 15 or 16 by reaction of the alcoholfunction in a compound of formula (I) with the group Y in the compoundof formula (II), optionally in the presence of catalyst wherein formula(I) isR_(f)—B—Ro—Z in which: R_(f) represents a perfluorinated alkyl radicalwith a straight or branched chain comprising 1 to 20 carbon atoms; Brepresents a bivalent group which may comprise 1 to 3 atoms of oxygen,sulfur and/or nitrogen; Ro represents 1 to 100 oxyalkylene groupsconnected to the group B via a carbon atom; and Z is a hydrogen atom or,when B carries a hydroxyl group, a linear or branched chain alkyl groupcomprising 1 to 6 carbon atoms; and wherein formula (II) is

in which: m is a whole number from 0 to 10; R represents, eachindependently from the other, a linear or branched alkyl groupcomprising 1 to 6 carbon atoms; p is a whole number from 0 to 2; Arepresents, each independently from the other, a halogen, or an alkoxygroup comprising 1 to 6 carbon atoms; and Y represents a groupcomprising an isocyanate, epoxy, carboxylic acid or alcohol function, Ycan also represent Si(R_(p))(A)_(3-p) when m is different from zero, anda group A when m is equal to zero.
 18. Surface treatment processcomprising the step of: i) applying a composition according to claim 1to a substrate being treated in the presence of a hydrolysis agent forthe alkoxysilane or halogenosilane groups present.
 19. Process accordingto claim 18 which comprises an additional step of: ii) thermal treatmentof the substrate obtained in step (i) at a temperature comprised between50 and 200° C. for a period of time comprised between 1 second and 24hours.
 20. Process according to claim 18 in which the hydrolysis agentis water.
 21. Treated substrate obtained by the process according to anyof the claims 18 to
 20. 22. Treated substrate according to claim 21, inwhich the substrate is chosen among glass, polymethyl methacrylate andpolycarbonate.